Startup founder, now what? Recruitment advice.


Long time lurker. Would appreciate some insight from the community.

I'm been an operator for four years having been a two-time co-founder, achieving venture-backing both times. In aggregate raising $6m seed capital.

I attended a target school in the UK (Oxbridge) for undergraduate and garnered limited experience (short internship in venture capital) before entering the start-up game.

I left my last start-up due to pragmatic reasons with the support of my team and investors: the company pivoted radically into a new geography and we are cash constraint so made some hard decisions.

I have transaction experience through micro M&A transactions as part of start-up growth strategy (acquiring another brand / marketing channels) but these were $300k - $1m transactions for small EBITDA positive companies.

I am capable of hard work and long hours don't faze me, and I want to learn hard core financial modelling and have transaction exposure. Naturally, I'd like to get on the analyst track at an IB but due to my age and experience I am not convinced I am a target hire and will do poorly in typical analyst recruitment cycles, especially at a BB.

VC is an option but the market is not great, and while I'm good at it, I don't want a career built entirely around origination / relationship management and miss out on drilling down on core skills that can be foundational career-wise. 

Does anyone have any advice or been in the same position? Are there any realistic access points for early-stage IB without going to b school?

Been trying to figure this out on my own for a while...

Comments (11)

  • Intern in HF - EquityHedge

Master's is probably your only bet tbh

  • 1
m_1, what's your opinion? Comment below:

Some other ideas since I think you're right, and IMO you'll have a lot of trouble working in a normal environment again.

1. Start an agency/freelance consulting. Very easy to get to ~$20k - $50k a month in FCF. Use the $$$s to fund something with real EV potential.

2. Ping a few friends with companies  doing ~$20m - $200m and join as Chief of Staff or some sort of intrapreneurial role. I would take a very low salary and ask for compensation largely based on performance targets. I would do the leg work to build these targets.

  • Associate 3 in PE - Other

can you elaborate on the agency? 

corporate_slave, what's your opinion? Comment below:

Just so I am understanding right, you raised a good amount of capital, ran teams, and are still un-hireable? You should have a unique technical/management skillset right?

anon-anon-anon-anon, what's your opinion? Comment below:

IB isn't as technical or "foundational" as you may think. Don't bother with it!

I was a trader before getting into venture and have a lot of friends in IB so I'd say I'm reasonably well-informed when I tell you absolutely do not waste your time with IB.

If you have the stomach to deal with the risk and uncertainty of founding a start-up, don't jump ship now.

Found another co or join a great co that you respect. Being an entrepreneur will likely pay more and teach you more in the long run. 

Working on starting my own co this year so I know how scary it can be, but in my opinion the road less traveled is usually worth it.

  • Works at Goldman Sachs

I like the bolding, anon-anon-anon-anon. I agree with your points. IB wasn't designed for analysts to "gain skills" and "learn". It was designed to hire cheap labor to grind through all the process work. 

That doesn't mean you don't learn anything in IB. But I think OP should definitely consider if it's worth his time at this point. People who have previously operated will often find the work in IB to be mind-numbing and intolerable. 

Most Helpful
APAE, what's your opinion? Comment below:

You've traveled through the murky depths of creating something from nothing .. twice.

Why on earth would you want to go through something as pedestrian as investment banking? 

Take your time and find another idea you have conviction in. As a repeat founder, you are actually in the driver's seat. There are so many communities for co-founder dating. Antler is a big one with presence in London. You are going to have people pitching you their ideas. You're the one who has experience raising funding. You've successfully done acquihires and acquisitions. You haven't flamed out. People will offer you half of their company because they're scared to do it alone. 

Seed is doing fine as a stage right now. Valuations have come back a bit towards reality, but you can still raise $5m pre-revenue if you have the basics (large market, initial customer validation, product thesis or ideally demo, and a strong team). It's just not happening on a $50m post like it was a year ago.

Your 'core skills' to drill down on are all operational. Each time you start a company, you do it with fewer mistakes than the last time. Why you'd want to walk away from a smarter-you running a company again is not something I understand.

Don't get a Master's. Don't go to business school. Spend three months doing four meetings a day with people in startups. Honestly, just cold email or Twitter or LinkedIn message people at interesting companies. Recent YC admits, not-so-recent YC admits who have raised a Series A or B, people who just announced an acquisition to a BigCo. Find smart people in the VP or 'Head of' positions just below the founder or C-level roles. Learn what they're excited about. Then take half of what you'd have spent on tuition and do three months in San Francisco and three months in New York. Meet as many of those people in person as you can, as well as all the people they suggest you meet. This will compound. Go to community events. There are too many happening to keep track of, you'll have a full calendar.

There is zero chance that after the better part of a year doing this you'll fail to have an idea for something you'd be excited to work on percolate through your brain. Congrats, you know the game from here. Do investor meetings (it's way easier in the States than the UK, you cannot fathom how much more money is sloshing around at the early stage here). Build a round. Only here it's not $250-500k checks for a $2m round. It's $1-2m checks for a $5m round, and that's if you don't hit it with someone who wants to do the whole thing. 

Banking is such a waste for you. Don't spend any more mental energy on it. 

Congrats on your success so far. Lean into it harder, man. 

I am permanently behind on PMs, it's not personal.

  • 14
  • Investment Analyst in HF - Event

Please disabuse yourself of the notion that "hardcore financial modelling" and "transaction exposure" are foundational skillset for your career. As someone who is on this conventional path you describe with IB/PE/HF exposure, just know that these are myths created and sold by pure-play IB/PE people who have no other viable skillset or industry expertise and thus add no value outside of pretending to do something important in Excel.

If you truly wish to gain a useful financial skill, learn how accounting works. There are a million resources out there whether it's video, book, courses. Just teach yourself how the income statement, cash flow, and balance sheet connect and what changes in each line item means for the business - this is the most useful knowledge you can get in running a company if it gets past the startup stage.

You've been warned. Do NOT prioritize learning "financial modeling" - which is not as useful of a skillset as you think it is, you've just been sold that it is. Given your abilities, you are better off letting a junior analyst at some bank do this for you for free when you are raising for your next company - not worth your time.

blackbrick, what's your opinion? Comment below:

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